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The liner notes for Degradation Trip Volumes 1 & 2 include an article by Don Kaye entitled "A Long, Strange Trip." This has Kaye describing the album's style and features quotes from Jerry Cantrell regarding its development and final release as a double album. Cantrell described the initial plans for the album:

"We probably had thirty-plus ideas - it could have been a triple record, you know what I mean? When I was making the record, my co-producer actually gave me George Harrison's triple record (All Things Must Pass), which is one of the coolest things anyone's ever given me. So yeah, this was intended to come out as Degradation Trip Volumes 1 & 2"

The label executives commended Cantrell's ambition but showed uneasiness toward the idea of a double album. Since Cantrell had already spent a year searching for a label that would take his album, he compromised and condensed his work on the promise that later on it would be released in its entirety.[3]

For about four months in 1998, Cantrell locked himself in his home to write the 25 songs. He noted that much of the songwriting was inspired by the demise of Alice in Chains, describing it as "looking at a situation where I had to move on, and not really being happy about it. . . So it was just coming to grips with all that stuff - and I'm still doing it, especially now that Layne's gone." Consequently, Degradation Trip boasts various dark themes and bleak visuals. Songs like "Bargain Basement Howard Hughes" and "Pig Charmer" directly relate to the relationship between Cantrell and former bandmate Layne Staley. "Owned" and "Pro False Idol" question the career of Cantrell and his status as a musician, while "Feel the Void" and "31/32" explore the concept of lives wasted. Cantrell elaborated, "Throughout the process of making this record, I often wondered at times whether I was insane or not. Sitting here, thinking back on it now, I probably had my moments." He also noted, however, the satisfaction in having released the album as he wanted and being able to put all of the intimate expression to bed.